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Paper | Regular issue | Vol 65, No. 12, 2005, pp.2861-2870
Published online, 14th October, 2005
DOI: 10.3987/COM-05-10507
Reactions of 4-Pentenoic Acid with Sulfenyl Cations Generated Electrochemically from Bisquinolinyl and Bispyridinyl Disulfides

Krzysztof Marciniec, Andrzej Maslankiewicz,* Maria J. Maslankiewicz, and Zbigniew Ciunik

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska 4, 41-200 Sosnowiec, Poland

Abstract

Lactonization of 4-pentenoic acid to 5-(azinylthio)methyloxolan-2-ones (8) was performed by addition of electrochemically generated azinylsulfenyl cations starting from the respective 3,3’-bis(pyridinyl or quinolinyl) disulfides (2) or (5) and 4,4’-bis(7-chloroquinolinyl or 3-methylthioquinolinyl) disulfides (6b), (6c) and using a bromide ion as a redox catalyst. Sulfenyl cations generated in the same manner from 2,2’-bispyridinyl and 2,2’-bisquinolinyl disulfides (1) or (4) reacted with 4-pentenoic acid to form thiazolo[3,2-a]pyridinio- or quinoliniopropanoate (9a) or (9b). In the case of 8,8’-bisquinolinyl disulfide (7), oxolan-2-one (8e) was accompanied by 2,3-dihydro-1,4-thiazinequinolinio derivative (10). 4,4’-Bis(pyridinyl nor quinolinyl) disulfides (3) and (6a) did not give such products.